We are looking for a deeply technical, collaborative engineering leader to shape how an engineering organization operates, modernizes, and scales.

The Head of Engineering Strategy will own and drive technical strategy, engineering modernization, standards, and major cross-team initiatives. This person will work closely with experienced senior engineers and technical leads, bringing strong technical leadership, modern engineering practices, and clear execution.

This is not a traditional people-management role. The focus is on technical leadership across the engineering organization—bringing strong engineering voices together, establishing direction, driving adoption, and ensuring important initiatives move from discussion to implementation.

The role reports directly to the VP of Product & Engineering.

What You’ll Do

• Drive engineering modernization, including AI-assisted development, modern engineering workflows, and emerging technologies that improve speed, quality, and developer effectiveness.

• Establish and drive adoption of engineering standards around unit testing, automated testing, code review, CI/CD, release processes, documentation, and development practices.

• Lead cross-team technical and architectural discussions, evaluate tradeoffs, establish direction, and drive decisions through implementation.

• Evaluate new technologies, tools, frameworks, and engineering approaches, taking promising ideas from experimentation through successful adoption.

• Bring senior engineers and technical leads together around important cross-team initiatives and ensure discussions result in clear decisions, ownership, and follow-through.

• Partner with technical leaders to strengthen reliability, observability, performance, infrastructure, environments, backups, and overall platform health.

• Identify areas where additional technical expertise or specialized roles would benefit the organization.

• Serve as a trusted technical partner to senior engineering leadership on technical strategy and organizational improvement.

What We’re Looking For

• Strong hands-on software engineering background, with the ability to review code and engage deeply in technical discussions.

• Significant experience providing senior technical leadership across multiple engineering teams.

• Strong understanding of software architecture, engineering practices, and scalable SaaS systems.

• Strong awareness of current and emerging technologies, including AI-assisted development, developer tooling, frameworks, cloud platforms, and modern software-development practices.

• Experience with automated testing, CI/CD, observability, reliability, and cloud-based SaaS environments.

• Ability to lead and influence highly experienced engineers without relying on formal reporting authority.

• Strong technical judgment and the ability to turn complex or competing viewpoints into clear direction and practical action.

• Excellent communication skills, including the ability to explain complex technical topics to non-engineering leadership.

• Proven track record of driving engineering-wide initiatives from idea through adoption and implementation.

• Ability to combine strong technical opinions with respect for existing systems, institutional knowledge, and experienced engineering teams.

What Success Looks Like

Within the first year:

• AI-assisted development practices are being used effectively and consistently across Engineering.

• Unit and automated testing have a clear, practical strategy and are being adopted across teams.

• Engineering standards and development practices are more consistent across the organization.

• New technologies and engineering tools are evaluated and adopted more quickly when they provide meaningful value.

• Senior engineering discussions consistently result in clear decisions, ownership, and implementation.

• Important technical improvements continue moving forward alongside feature development.

• Engineering becomes more efficient while maintaining or improving quality, stability, and reliability.

The Ideal Candidate

You are deeply technical, highly current, pragmatic, and execution-oriented. You actively stay ahead of changes in software engineering, AI, tooling, and development practices rather than waiting for established approaches to become industry standard.

You are comfortable working with experienced engineers who may have strong and differing opinions. You listen carefully, challenge assumptions, and know when to push toward a decision.

You lead through technical credibility, collaboration, sound judgment, and execution, with a strong backbone and low ego.